Palladium-catalyzed oxidative cross-coupling of azole-4-carboxylates with indoles: an approach to the synthesis of pimprinine

Haipin Zhou; Kuo Gai; Aijun Lin; Jinyi Xu; Xiaoming Wu; Hequan Yao

doi:10.1039/c4ob01844c

Palladium-catalyzed oxidative cross-coupling of azole-4-carboxylates with indoles: an approach to the synthesis of pimprinine

Org Biomol Chem. 2015 Jan 28;13(4):1243-8. doi: 10.1039/c4ob01844c. Epub 2014 Dec 1.

Authors

Haipin Zhou¹, Kuo Gai, Aijun Lin, Jinyi Xu, Xiaoming Wu, Hequan Yao

Affiliation

¹ State Key Laboratory of Natural Medicines and Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing, 210009, P. R. China. xmwu@cpu.edu.cn hyao@cpu.edu.cn.

PMID: 25434639
DOI: 10.1039/c4ob01844c

Abstract

An efficient and straightforward method for the production of 5-(3-indolyl)azoles incorporating the privileged structures indoles and azoles via palladium-catalyzed double C-H bond cleavage under mild conditions was disclosed. As expected, this protocol provided an easy method for the synthesis of indole alkaloids pimprinine and WS-30581 A in moderate yields.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Azoles / chemistry*
Carboxylic Acids / chemistry*
Catalysis
Chemistry Techniques, Synthetic
Indoles / chemistry*
Oxazoles / chemical synthesis*
Oxazoles / chemistry
Oxidation-Reduction
Palladium / chemistry*
Stereoisomerism
Substrate Specificity

Substances

Azoles
Carboxylic Acids
Indoles
Oxazoles
pimprinine
Palladium